Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica

Detalhes bibliográficos
Autor(a) principal: Franco, Maynne Duarte Suriani
Data de Publicação: 2023
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da UFU
Texto Completo: https://repositorio.ufu.br/handle/123456789/37839
http://doi.org/10.14393/ufu.di.2023.236
Resumo: In the present work, we investigated the photophysical properties, the interaction with the Human Serum Albumin (HSA) protein, incorporation, cytotoxicity and phototoxicity in HeLa-type tumor cells of two novel derivatives of Protoporphyrin IX (PpIX) for application in Photodynamic Therapy (PDT). The modification of the structure occurred in the ramifications of PpIX where portions of piperazine or morpholine were added in order to promote a synergistic effect, increasing its photoactivity and, consequently, its phototoxicity. For this, the derivatives named PpIX-Methyl-Piperazine and PpIX-Morpholine were characterized by spectroscopic techniques and photophysical studies such as the determination of the molar absorptivity coefficient, quantum yield of fluorescence and singlet oxygen, as well as possible reactions of photobleaching using LED performing the comparison with the precursor molecule PpIX, where it was possible to observe that the modifications carried out did not bring great variations in the spectroscopic and photophysical characteristics of the new PpIX derivatives. Aggregation studies in water/methanol and water/DMSO mixtures were also explored, in order to understand the behavior of these molecules in aqueous medium, the majority environment of living cells, where it was possible to perceive that changes in the ramifications of PpIX brought improvement in solubility of PpIX-Methyl-Piperazine and PpIX-Morpholine in aqueous media compared to PpIX. The degree of interaction of HSA with porphyrin compounds was also studied, since it allows the binding of a wide range of endogenous and exogenous compounds and allows the transport of molecules within the human body where an interaction was observed only with PpIX- Methyl-Piperazine. Furthermore, a study of incorporation, cytotoxicity and phototoxicity in HeLa-type tumor cells was performed to evaluate the applicability of these new compounds in PDT, where it was possible to observe a larger phototoxicity of both molecules in comparison with PpIX, making the new molecules excellent candidates for Photodynamic Therapy.
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spelling Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmicaProtoporphyrin IX derivatives functionalized with piperazine and morpholine in order to potentiate the activity photodynamicTerapia FotodinâmicaPhotodynamic TherapyPorfirinasPorphyrinsFototoxicidadePhototoxicityCélulas tumoraisTumor cellsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn the present work, we investigated the photophysical properties, the interaction with the Human Serum Albumin (HSA) protein, incorporation, cytotoxicity and phototoxicity in HeLa-type tumor cells of two novel derivatives of Protoporphyrin IX (PpIX) for application in Photodynamic Therapy (PDT). The modification of the structure occurred in the ramifications of PpIX where portions of piperazine or morpholine were added in order to promote a synergistic effect, increasing its photoactivity and, consequently, its phototoxicity. For this, the derivatives named PpIX-Methyl-Piperazine and PpIX-Morpholine were characterized by spectroscopic techniques and photophysical studies such as the determination of the molar absorptivity coefficient, quantum yield of fluorescence and singlet oxygen, as well as possible reactions of photobleaching using LED performing the comparison with the precursor molecule PpIX, where it was possible to observe that the modifications carried out did not bring great variations in the spectroscopic and photophysical characteristics of the new PpIX derivatives. Aggregation studies in water/methanol and water/DMSO mixtures were also explored, in order to understand the behavior of these molecules in aqueous medium, the majority environment of living cells, where it was possible to perceive that changes in the ramifications of PpIX brought improvement in solubility of PpIX-Methyl-Piperazine and PpIX-Morpholine in aqueous media compared to PpIX. The degree of interaction of HSA with porphyrin compounds was also studied, since it allows the binding of a wide range of endogenous and exogenous compounds and allows the transport of molecules within the human body where an interaction was observed only with PpIX- Methyl-Piperazine. Furthermore, a study of incorporation, cytotoxicity and phototoxicity in HeLa-type tumor cells was performed to evaluate the applicability of these new compounds in PDT, where it was possible to observe a larger phototoxicity of both molecules in comparison with PpIX, making the new molecules excellent candidates for Photodynamic Therapy.CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorCNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPEMIG - Fundação de Amparo a Pesquisa do Estado de Minas GeraisIQUFU - Instituto de Química da Universidade Federal de UberlândiaUFU - Universidade Federal de UberlândiaDissertação (Mestrado)No presente trabalho, investigou-se as propriedades fotofísicas, a interação com a proteína Albumina Sérica Humana (HSA), incorporação, citotoxicidade e fototoxicidade em células tumorais do tipo HeLa de dois derivados inéditos da Protoporfirina IX (PpIX) para a aplicação na Terapia Fotodinâmica (TFD). A modificação da estrutura ocorreu nas ramificações da PpIX onde foi adicionado porções de piperazina ou morfolina a fim de promover efeito sinérgico, aumentando sua fotoatividade e, consequentemente sua fototoxicidade. Para isso, os derivados nomeados PpIX-Metil-Piperazina e PpIX-Morfolina foram caracterizados por técnicas espectroscópicas e estudos fotofísicos como, a determinação do coeficiente de absortividade molar, rendimento quântico de fluorescência e oxigênio singlete, assim como também, foram avaliadas possíveis reações de fotobranqueamento com uso do LED. Em comparação com a molécula precursora PpIX, foi possível observar que as modificações estruturais realizadas não trouxeram grandes variações nas características espectroscópicas e fotofísicas dos novos derivados da PpIX. Estudos de agregação em misturas de água/metanol e água/DMSO também foram explorados, para fim de compreender o comportamento destas moléculas em meio aquoso, ambiente majoritário de células vivas, onde foi possível perceber que as mudanças nas ramificações da PpIX trouxeram melhora na solubilidade da PpIX-Metil-Piperazina e PpIX-Morfolina em meio aquoso comparado a PpIX. Também foi estudado o grau de interação da HSA junto dos compostos porfirínicos, já que ela permite a ligação de uma ampla gama de compostos endógenos e exógenos e possibilita o transporte de moléculas dentro do corpo humano onde observou-se uma interação apenas com a PpIX-Metil-Piperazina. E ainda, realizou-se um estudo de incorporação, citotoxicidade e fototoxicidade em células tumorais do tipo HeLa para avaliar a aplicabilidade destes novos compostos na TFD, onde foi possível observar uma maior fototoxicidade de ambas as moléculas em comparativo com a PpIX, tornando as novas moléculas excelentes candidatos a Terapia Fotodinâmica.Universidade Federal de UberlândiaBrasilPrograma de Pós-graduação em QuímicaTsubone, Tayana Mazinhttp://lattes.cnpq.br/9697885201846175Rezende Júnior, Celso de Oliveirahttp://lattes.cnpq.br/7220061875015002Tudin, Kelly Aparecida Geraldo Yoneyamahttp://lattes.cnpq.br/4669225820474441Tasso, Thiago Teixeirahttp://lattes.cnpq.br/6831450941039180Franco, Maynne Duarte Suriani2023-05-11T11:58:27Z2023-05-11T11:58:27Z2023-04-13info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfFRANCO, Maynne Duarte Suriani. Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica. 2023. 101 f. Dissertação (Mestrado em Química) - Universidade Federal de Uberlândia, Uberlândia, 2023. DOI http://doi.org/10.14393/ufu.di.2023.236https://repositorio.ufu.br/handle/123456789/37839http://doi.org/10.14393/ufu.di.2023.236porhttp://creativecommons.org/licenses/by-nc-nd/3.0/us/info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFUinstname:Universidade Federal de Uberlândia (UFU)instacron:UFU2023-05-12T06:24:49Zoai:repositorio.ufu.br:123456789/37839Repositório InstitucionalONGhttp://repositorio.ufu.br/oai/requestdiinf@dirbi.ufu.bropendoar:2023-05-12T06:24:49Repositório Institucional da UFU - Universidade Federal de Uberlândia (UFU)false
dc.title.none.fl_str_mv Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
Protoporphyrin IX derivatives functionalized with piperazine and morpholine in order to potentiate the activity photodynamic
title Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
spellingShingle Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
Franco, Maynne Duarte Suriani
Terapia Fotodinâmica
Photodynamic Therapy
Porfirinas
Porphyrins
Fototoxicidade
Phototoxicity
Células tumorais
Tumor cells
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
title_full Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
title_fullStr Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
title_full_unstemmed Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
title_sort Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica
author Franco, Maynne Duarte Suriani
author_facet Franco, Maynne Duarte Suriani
author_role author
dc.contributor.none.fl_str_mv Tsubone, Tayana Mazin
http://lattes.cnpq.br/9697885201846175
Rezende Júnior, Celso de Oliveira
http://lattes.cnpq.br/7220061875015002
Tudin, Kelly Aparecida Geraldo Yoneyama
http://lattes.cnpq.br/4669225820474441
Tasso, Thiago Teixeira
http://lattes.cnpq.br/6831450941039180
dc.contributor.author.fl_str_mv Franco, Maynne Duarte Suriani
dc.subject.por.fl_str_mv Terapia Fotodinâmica
Photodynamic Therapy
Porfirinas
Porphyrins
Fototoxicidade
Phototoxicity
Células tumorais
Tumor cells
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
topic Terapia Fotodinâmica
Photodynamic Therapy
Porfirinas
Porphyrins
Fototoxicidade
Phototoxicity
Células tumorais
Tumor cells
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In the present work, we investigated the photophysical properties, the interaction with the Human Serum Albumin (HSA) protein, incorporation, cytotoxicity and phototoxicity in HeLa-type tumor cells of two novel derivatives of Protoporphyrin IX (PpIX) for application in Photodynamic Therapy (PDT). The modification of the structure occurred in the ramifications of PpIX where portions of piperazine or morpholine were added in order to promote a synergistic effect, increasing its photoactivity and, consequently, its phototoxicity. For this, the derivatives named PpIX-Methyl-Piperazine and PpIX-Morpholine were characterized by spectroscopic techniques and photophysical studies such as the determination of the molar absorptivity coefficient, quantum yield of fluorescence and singlet oxygen, as well as possible reactions of photobleaching using LED performing the comparison with the precursor molecule PpIX, where it was possible to observe that the modifications carried out did not bring great variations in the spectroscopic and photophysical characteristics of the new PpIX derivatives. Aggregation studies in water/methanol and water/DMSO mixtures were also explored, in order to understand the behavior of these molecules in aqueous medium, the majority environment of living cells, where it was possible to perceive that changes in the ramifications of PpIX brought improvement in solubility of PpIX-Methyl-Piperazine and PpIX-Morpholine in aqueous media compared to PpIX. The degree of interaction of HSA with porphyrin compounds was also studied, since it allows the binding of a wide range of endogenous and exogenous compounds and allows the transport of molecules within the human body where an interaction was observed only with PpIX- Methyl-Piperazine. Furthermore, a study of incorporation, cytotoxicity and phototoxicity in HeLa-type tumor cells was performed to evaluate the applicability of these new compounds in PDT, where it was possible to observe a larger phototoxicity of both molecules in comparison with PpIX, making the new molecules excellent candidates for Photodynamic Therapy.
publishDate 2023
dc.date.none.fl_str_mv 2023-05-11T11:58:27Z
2023-05-11T11:58:27Z
2023-04-13
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv FRANCO, Maynne Duarte Suriani. Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica. 2023. 101 f. Dissertação (Mestrado em Química) - Universidade Federal de Uberlândia, Uberlândia, 2023. DOI http://doi.org/10.14393/ufu.di.2023.236
https://repositorio.ufu.br/handle/123456789/37839
http://doi.org/10.14393/ufu.di.2023.236
identifier_str_mv FRANCO, Maynne Duarte Suriani. Derivados de Protoporfirina IX funcionalizadas com piperazina e morfolina visando potencializar a atividade fotodinâmica. 2023. 101 f. Dissertação (Mestrado em Química) - Universidade Federal de Uberlândia, Uberlândia, 2023. DOI http://doi.org/10.14393/ufu.di.2023.236
url https://repositorio.ufu.br/handle/123456789/37839
http://doi.org/10.14393/ufu.di.2023.236
dc.language.iso.fl_str_mv por
language por
dc.rights.driver.fl_str_mv http://creativecommons.org/licenses/by-nc-nd/3.0/us/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/3.0/us/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidade Federal de Uberlândia
Brasil
Programa de Pós-graduação em Química
publisher.none.fl_str_mv Universidade Federal de Uberlândia
Brasil
Programa de Pós-graduação em Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFU
instname:Universidade Federal de Uberlândia (UFU)
instacron:UFU
instname_str Universidade Federal de Uberlândia (UFU)
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institution UFU
reponame_str Repositório Institucional da UFU
collection Repositório Institucional da UFU
repository.name.fl_str_mv Repositório Institucional da UFU - Universidade Federal de Uberlândia (UFU)
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